Acid-Triggered, Acid-Generating, and Self-Amplifying Degradable Polymers

Miller, Kali A.; Morado, Ephraim G.; Samanta, Shampa R.; Walker, Brittany A.; Nelson, Arif Z.; Sen, Samya; Tran, Dung T.; Whitaker, Daniel J.; Ewoldt, Randy H.; Braun, Paul V.; Zimmerman, Steven C.

doi:10.1021/jacs.8b07705

Acid-Triggered, Acid-Generating, and Self-Amplifying Degradable Polymers

Journal Article · Wed Jan 30 04:00:00 EST 2019 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.8b07705· OSTI ID:1606377

^[1]; Morado, Ephraim G. ^[2]; Samanta, Shampa R. ^[2]; Walker, Brittany A. ^[2]; ^[2]; Sen, Samya ^[2]; Tran, Dung T. ^[2]; Whitaker, Daniel J. ^[2]; ^[2]; ^[2]; ^[2]

Univ. of Illinois at Urbana-Champaign, IL (United States); University of Illinois at Urbana-Champaign
Univ. of Illinois at Urbana-Champaign, IL (United States)

We describe the 3-iodopropyl acetal moiety as a simple cleavable unit that undergoes acid catalyzed hydrolysis to liberate HI (pK_a~ -10) and acrolein stoichiometrically. Integrating this unit into linear and network polymers gives a class of macromolecules that undergo a new mechanism of degradation with an acid amplified, sigmoidal rate. This trigger-responsive self amplified degradable polymer undergoes accelerated rate of degradation and agent release.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Illinois at Urbana-Champaign, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-07ER46471

OSTI ID:: 1606377

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 7 Vol. 141; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited By (3)

Synthesis and properties of degradable gels and porous polymers including acetal group in the network structure by addition reaction of multi-functional phenols and divinyl ether compounds Naga, Naofumi; Hasegawa, Kazuma; Nageh, Hassan Polymer Bulletin, Vol. 77, Issue 11 https://doi.org/10.1007/s00289-019-03033-1	journal	December 2019
Orthogonally functionalizable polyacetals: a versatile platform for the design of acid sensitive amphiphilic copolymers Moreno, Adrian; Lligadas, Gerard; Ronda, Juan Carlos Polymer Chemistry, Vol. 10, Issue 38 https://doi.org/10.1039/c9py01107b	journal	January 2019
Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s Blake, Timothy R.; Ho, Wilson C.; Turlington, Christopher R. Chemical Science, Vol. 11, Issue 11 https://doi.org/10.1039/c9sc05267d	journal	January 2020

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Hydrogels
Hydrolysis
Polymer degradation
Polymers

Acid-Triggered, Acid-Generating, and Self-Amplifying Degradable Polymers

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